Potassium Carbonate → cis-3-Benzyl-7-(2-fluoro-4-nitrophenyl)-3,7-diazabicyclo[3,3,0]octane

HRID 2288761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2288761
[CH2:1]([N:8]1[CH2:15][C@@H:14]2[C@@H:10]([CH2:11][NH:12][CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1F.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:8]1[CH2:9][C@@H:10]2[C@@H:14]([CH2:13][N:12]([C:22]3[CH:21]=[CH:20][C:19]([N+:24]([O-:26])=[O:25])=[CH:18][C:17]=3[F:16])[CH2:11]2)[CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 1514450rel-(3aR,6aS)-Octahydro-2-(phenylmethyl)pyrrolo(3,4-c)pyrrole

Produkt 1

HCID 21969626cis-3-Benzyl-7-(2-fluoro-4-nitrophenyl)-3,7-diazabicyclo[3,3,0]octane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of cis-3-benzyl-3,7-diazabicyclo[3.3.0]octane (0.35 g, 1.73 mmol) in acetonitrile (10 mL) is added 3,4-difluoronitrobenzene (0. 19 mL, 1. 73 mmol) and potassium carbonate (0.60 g, 4.33 mmol) under a nitrogen atmosphere at ambient temperature. The reaction is stirred 15 hours, concentrated in vacuo, and diluted with ethyl acetate (100 mL). The organic phase is washed with water (3×20 mL) and saline (20 mL), dried over sodium sulfate, concentrated in vacuo, and chromatographed on silica gel (230-400 mesh, 100 mL), eluting with chloroform/methanol (99/1). The appropriate fractions are combined (Rf =0.49, TLC, chloroform/methanol, 95/5) and concentrated in vacuo to give the title compound, NMR (CDCl3) 7.94, 7.88, 7.29, 6.62, 3.73, 3.64, 3.44, 2.97, 2.75, 2.55.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additiondiluted with ethyl acetate (100 mL)
  3. washThe organic phase is washed with water (3×20 mL) and saline (20 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel (230-400 mesh, 100 mL)
  7. washeluting with chloroform/methanol (99/1)
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9138e89a8cad436ab9a5692c1d0ae950
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06090820

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